Synlett 2023; 34(01): 63-66 DOI: 10.1055/a-1937-9185
Potassium Persulfate/Tributylamine-Mediated Alkylation/Annulation of N -Arylacrylamides with Alkyl Iodides
Huimin Chen
,
Zetian Sun
,
Hui Yang
,
Fenghua Mao
,
Xinhuan Yan
,
Xiaoqing Li∗
,
Xiangsheng Xu∗
We thank the Natural Science Foundation of Zhejiang Province (LY21B020008) for financial support.
Abstract
We report a catalyst-free method for the alkylation/annulation of N -arylacrylamides to give the corresponding 3-alkyl-2-oxo-2,3-dihydro-1H -indoles by using alkyl iodides as precursors of alkyl radicals. These reactions occur at moderate temperatures and are mediated by easily accessible K2 S2 O8 and Bu3 N.
Key words
arylacrylamides -
cyclization -
oxindoles -
halogen-atom transfer -
alkylation
Supporting Information
Supporting information for this article is available online at https://doi.org/10.1055/a-1937-9185.
Supporting Information
Publikationsverlauf
Eingereicht: 23. Juli 2022
Angenommen nach Revision: 06. September 2022
Accepted Manuscript online: 06. September 2022
Artikel online veröffentlicht: 17. Oktober 2022
© 2022. Thieme. All rights reserved
Georg Thieme Verlag KG Rüdigerstraße 14, 70469 Stuttgart, Germany
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tert -Butyl 4-[(1,3-Dimethyl-2-oxo-2,3-dihydro-1H -indol-3-yl)methyl]piperidine-1-carboxylate (3a); Typical Procedure
A dried reaction tube charged with 1a (35 mg, 0.2 mmol), 2a (124.5 mg, 0.4mmol), and K2 S2 O8 (0.6 mmol) was evacuated and backfilled with argon three times. MeCN (1.6 mL), H2 O (0.4 mL), and Bu3 N (1 mmol) were injected into the tube by syringe, and the mixture was heated at 70 ℃ for 12 h. The crude product was purified by column chromatography [silica gel, PE–EtOAc (4:1)] to give a brown oil; yield: 55.4 mg (80%); Rf
= 0.3 (PE–EtOAc, 4:1).
1 H NMR (500 MHz, CDCl3 ): δ = 7.28 (d, J = 7.7 Hz, 1 H), 7.16 (d, J = 7.4 Hz, 1 H), 7.07 (t, J = 7.5 Hz, 1 H), 6.85 (d, J = 7.8 Hz, 1 H), 3.84 (s, 2 H), 3.22 (s, 3 H), 2.51–2.32 (m, 2 H), 1.98 (dd, J = 14.1, 6.2 Hz, 1 H), 1.76 (dd, J = 14.1, 5.4 Hz, 1 H), 1.39 (s, 9 H), 1.32 (s, 3 H), 1.25 (s, 1 H), 1.15–1.00 (m, 3 H), 0.91–0.83 (m, 1 H).
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